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Record W4417500693 · doi:10.1021/acscatal.5c06523

Indigo Formation as a Predictor of Non-Native Aromatic Hydroxylation in Cytochrome P450 BM3

2025· article· en· W4417500693 on OpenAlexafffund
Jonathan N. Besna, Douglas J. Fansher, Donya Valikhani, Olivier Rousseau, Claudèle Lemay-St-Denis, Guillaume Lamoureux, Joelle N. Pelletier

Bibliographic record

VenueACS Catalysis · 2025
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicPharmacogenetics and Drug Metabolism
Canadian institutionsUniversité du Québec à MontréalCegep Edouard MontpetitUniversité de MontréalPROTEOCentre in Green Chemistry and Catalysis
FundersFonds de recherche du QuébecHydro-QuébecNatural Sciences and Engineering Research Council of CanadaCanada Research Chairs
KeywordsHydroxylationCytochrome P450Substrate (aquarium)Indole testEnzymeMutagenesisReactivity (psychology)Active site

Abstract

fetched live from OpenAlex

Screening cytochrome P450 BM3 enzyme for specific non-native reactivity is challenging. This enzyme is natively promiscuous in hydroxylation and epoxidation reactions and directed evolution has broadened its scope of reactivity, making it valuable in synthetic schemes. To accelerate discovery of further targets of reactivity, this study investigates indigo formation as a cost-effective predictive marker for hydroxylation of non-native aromatic compounds. Following site-saturation mutagenesis at 42 active-site positions, we identified 142 previously unreported indigo-producing variants that were point-substituted at one of 23 positions, substantially increasing the database of indigo-producing variants. From this pool, 81 well-expressed indigo-positive and 46 indigo-negative variants were screened for hydroxylation of 17 aromatic compounds that are not native substrates of P450 BM3 using the colorimetric 4-aminoantipyrine assay; 10 of the compounds were found to be good substrates for hydroxylation by many variants. Although MD simulations identified no property clearly distinguishing indigo-positive from indigo-negative variants, we found indigo-positive variants to exhibit significantly higher activity and substrate promiscuity, on average. For instance, relative to wild-type P450 BM3, 93% of indigo-positive variants displayed ≥ 7-fold increased hydroxylation of 1-Br-naphthalene compared to only 9% of indigo-negative variants. Increased substrate promiscuity is illustrated by Spearman correlations of reactivity, reaching ≥ 0.7 for 12 substrate pairs. Furthermore, the 10 variants ranked most promiscuous and most active for aromatic hydroxylation are all indigo-positive. We thus found that screening for indigo formation by visualizing E. coli colonies allowed reliable identification of all the top point-substituted variants, with a high hit-rate of increased substrate promiscuity and activity increased up to 167-fold relative to the native enzyme. This efficient screen will serve as a powerful primary tool to accelerate the expansion of the functional repertoire of P450 BM3 variants. Our findings are presented in machine-readable format to aid ulterior machine learning, providing a foundation for computational advances to predict further substrate-variant combinations.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.092
Threshold uncertainty score0.813

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.038
GPT teacher head0.407
Teacher spread0.369 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2025
Admission routes2
Has abstractyes

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